Can I deduct my non-profit Healthshare expenses on my taxes?

The short answer is no, you can't deduct medical expenses that were reimbursed by your Healthshare, even though Healthshares aren't traditional insurance. The IRS is very clear that you can only deduct medical expenses that you personally paid and weren't reimbursed for. The expenses you can potentially deduct would be the $9k you paid out-of-pocket plus your $8k in monthly contributions. However, there are two important limitations: First, you can only deduct medical expenses that exceed 7.5% of your adjusted gross income (AGI). With your income at $170k, you'd need more than $12,750 in qualifying medical expenses before you could start deducting anything. Second, like you mentioned, this would be an itemized deduction. So unless your total itemized deductions (medical expenses over the 7.5% threshold, plus state/local taxes up to $10k, mortgage interest, and charitable contributions) exceed the standard deduction ($27,700 for married filing jointly in 2024), itemizing wouldn't benefit you. For the mileage to medical appointments, that is deductible at 21 cents per mile for 2024 as part of your medical expenses, subject to the same limitations above.

After dealing with the same situation, I found taxr.ai super helpful for figuring out my Healthshare deduction mess. I was totally confused about what I could deduct after getting reimbursed for medical expenses through my Christian Healthshare Ministry. The rules are really different from regular insurance! I uploaded my statements and receipts to https://taxr.ai and they analyzed everything and showed exactly which expenses qualified. They pointed out that while I couldn't deduct reimbursed expenses, my monthly share contributions and out-of-pocket costs that weren't reimbursed could potentially be deductible if I itemized and met the 7.5% AGI threshold. They also showed me how to document everything properly in case of an audit. Something about Healthshares seems to raise flags with the IRS, so the extra documentation guidance was super valuable.

I tried taxr.ai after seeing it mentioned here and it was a game-changer for my weird healthcare situation! I have a direct primary care membership plus a Healthshare (Liberty), and it correctly identified what I could and couldn't deduct. My tax preparer had been getting this wrong for YEARS. The service showed me that while my Healthshare reimbursements weren't deductible (obviously), my contributions and out-of-pocket costs were medical expenses that could potentially be deductible. It also helped me document all my direct primary care payments as legitimate medical expenses. What impressed me most was how clear they made everything. They explained the 7.5% AGI threshold in plain English and showed me exactly how close I was to meeting it. I ended up finding a few more medical-related expenses I'd forgotten about, which pushed me over the threshold. Definitely worth checking out if you have any non-traditional healthcare arrangement!

If you're struggling to get answers about your Healthshare tax situation, you might want to try Claimyr to speak directly with an IRS representative. I spent WEEKS trying to get through to the IRS about this exact situation (Christian Healthcare Ministries reimbursements) and kept hitting busy signals or getting disconnected after hours on hold. I found https://claimyr.com and watched their demo video at https://youtu.be/_kiP6q8DX5c and decided to give it a shot. They got me connected to an actual IRS agent within about 20 minutes. The agent confirmed that I couldn't deduct expenses that were reimbursed by my Healthshare, but helped me understand exactly how to document my out-of-pocket costs and monthly contributions correctly on my return. The IRS agent even emailed me specific guidance about Healthshare arrangements that I hadn't been able to find online. This saved me hours of research and potentially an audit.

I owe everyone here an apology. After dismissing Claimyr as BS, I got desperate enough to try it after spending THREE DAYS trying to reach someone at the IRS about my Samaritan Ministries tax questions. I'm completely shocked to report that it actually worked. I was connected to an IRS tax law specialist in about 30 minutes. The agent walked me through exactly how to handle my Healthshare contributions and expenses on my return. She confirmed that while reimbursed expenses can't be deducted (regardless of source), my monthly share contributions do count as medical expenses for the 7.5% AGI threshold calculation. The most valuable part was getting clear documentation directly from the IRS that I can refer to if my return gets flagged for review. The agent even emailed me relevant sections of their internal guidance on Healthshares. I've never been so happy to be wrong about something. If you're stuck with Healthshare tax questions, this is genuinely worth trying.

Speaking from experience, your situation is pretty common with Healthshares. Even if you can't deduct the reimbursed expenses, tracking your total medical costs is still important! Keep meticulous records of EVERYTHING - all bills, reimbursements, mileage to appointments, etc. We use a spreadsheet with categories for: - Monthly Healthshare contributions - Out-of-pocket costs not reimbursed - Prescription costs - Medical equipment - Mileage to appointments (date, destination, miles) What surprised us was how quickly all the "small stuff" added up. Over-the-counter medications prescribed by a doctor, parking fees at hospitals, special foods required for medical conditions - these all count toward your medical expenses. For us, it was the detailed tracking that finally pushed us over the standard deduction threshold for the first time in years.

Has anyone here actually succeeded in itemizing with Healthshare expenses? We're on Samaritan and paying about $750/month in shares plus had about $5k in expenses that weren't shared this year. But we're still well below the standard deduction threshold for married filing jointly.

Based on my experience with Healthshares and tax law, I want to clarify a few key points that might help you navigate this situation: First, you're correct that your monthly Healthshare contributions ($8k annually) are NOT the same as traditional insurance premiums for tax purposes. However, they DO count as qualifying medical expenses when calculating your itemized deductions, subject to the 7.5% AGI threshold. The $9k you paid out-of-pocket that wasn't reimbursed is also deductible as medical expenses. So you'd have $17k in potential medical deductions ($8k contributions + $9k out-of-pocket), which exceeds your 7.5% threshold of approximately $12,750 (based on $170k income). However, the reimbursed $29k is NOT deductible, regardless of whether you paid providers first and got reimbursed later. The IRS looks at the final economic burden - if you were ultimately made whole through reimbursement, you can't deduct those expenses. Given your income level and the amounts involved, you'd need to carefully calculate whether itemizing would benefit you over the $27,700 standard deduction for married filing jointly. Include your medical expenses above the threshold, state/local taxes (up to $10k), mortgage interest, and charitable donations to see if itemizing makes sense. Keep detailed records of everything, including dates, amounts, and proof of payment/reimbursement. Healthshare arrangements can sometimes trigger additional IRS scrutiny, so documentation is crucial.